Espresso: Henrik Grim on Nassim Taleb and Black Swans

26 Jun 2026 · 5 min · 3 chapters

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In short

Henrik Grim discusses Nassim Taleb’s ideas—Black Swans, Anti-Fragile thinking, and barbell strategy—and how they apply to business building and venture investing, including risk management via revenue concentration.

Guest background

Henrik Grim is a VC who meets thousands of companies annually and invests in only a handful.

Key claims

Black swans are unpredictable and often involve luck; this mindset gives “inner peace” and encourages steady effort. Anti-fragility comes from holding opposing positions (barbell strategy): low-risk stability paired with high-risk upside. Probabilistic thinking should coexist with a clear vision.

Notable examples

He contrasts investing “no” to thousands of companies with the few that succeed; he also cites brands that concentrated 95%+ revenue with one wholesaler/grocer, then suffered when that partner was removed—arguing for diversified revenue sources (10–20 wholesalers plus on/off trade).

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Insights from Nassim Taleb

0:33 to 2:30

Exploring Nassim Taleb's concepts and how they apply to business building.

“so what have you picked up from Nassim Taleb and how have you applied that to your business because he's got a myriad of wonderful books.”

Barbell Strategy and Risk Management

2:30 to 4:47

Discussion on the barbell strategy and its implications for minimizing business risks.

“and maybe you'll get the black swan event for yourself.”

Revenue Concentration and Business Risks

4:47 to 5:40

Examining the impact of revenue concentration on business stability and growth.

“And then obviously having all your eggs in that basket can put you in a pretty tough spot.”
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Transcript

Automatic transcript. May contain errors.

0:00Nassim Taleb:Yes, yes, people. So the hungry reading list is here, right? If you listen to the podcast regularly, you know I love reading. I think books are the most beautiful thing in the world. As Stephen King said, they're teleportable magic or something like that. these books I whittled down my gargantuan bookshelf into 46 absolute 30 bangers the link is in the show notes to get the list whatever and it'll also make you a subscriber to our weekly newsletter which I think is sick so yeah get your fucking books buddy so what have you picked up from Nassim Taleb and how have you applied that to your business because he's got a myriad of wonderful books.

0:40Nassim Taleb:Yeah. I think Anti-Fragile, I've just reread Fooled by Randomness.

0:45Henrik Grim:Like, I just love the way he thinks. As a VC, I met thousands of companies every year. I said no to thousands of companies every year, not investing in them. And probably said yes to, you know, a handful at max. Now, I think some of the parallels to the sort of Black Swan sort of theory, I think sometimes gives me a little bit of sort of, I sort of look at business building a little bit in that sort of with the lens of Black Swans and that you don't necessarily always know and you can't always predict sort of how things are going to play out in your particular business and whether you're going to be the one that sort of ramps up really quickly and explodes and sort of does really well, or if you're going to be the one that sort of tapers off, Like, are you going to be the black swan business that does really well?

1:37Henrik Grim:To a great extent, you don't necessarily know. And to some extent, maybe you can't even control it. Like for many large companies, there's always this element of luck. Yeah. And I think if there's anything, I'd probably say that having, you know, spend time as a VC, having met thousands of amazing founders that are, you know, pushing so hard every day to build beautiful businesses, but still not making it or not being the right fit for our investment. I think the sort of black swan idea of you not necessarily being in control has almost given me a little bit of inner peace when it comes to building a business and just being respectful for the process in that you don't necessarily know exactly what's going to happen.

2:19Henrik Grim:You can't control everything. Like there's always an element of luck in any business. And so as long as you sort of keep chugging away on whatever you can do, then you'll be fine. and maybe you'll get the black swan event for yourself. Yeah. But, and I'm thinking about black swan mostly as positives.

2:37Nassim Taleb:Yeah, so I think black swan's negative, white swan's positive. White swan, fair enough. Yeah, yeah, yeah, yeah. That's why I sort of frame it. But it's interesting because it's like, again, one of his big things is barbell strategy, which is holding two opposing things at once. Right. That makes you anti-fragile, right? Yes. So like, for example, um like in the the way he describes it is investing right so it's like have have an um a big chunk of your proportion in in low risk bonds that are just going to keep taking away with some high risk stuff yeah those two opposing tensions make you anti-fragile it's the barbell strategy yeah and i think what you're saying there mate i completely agree it's like there's his his whole thing is probabilistic thinking, right?

3:21Nassim Taleb:Yeah. Versus deterministic. And I think that's a good barbell strategy. It's like be deterministic, but this is where we're going. Yep. This is how Spotify is going to get built. This is the vision. But then actually be pretty loose, fluid in the sense that something's going to go your way and a lot's going to go not your way. Exactly. But I think where people get bogged down is you're one or the other.

3:42Henrik Grim:Yeah. It's interesting. And I think it relates a lot to many other brands we're working with in sort of how they minimize risk for themselves. I think one of the core, when we're judging whether to offer funding, for example, to a brand, one of the core things we're looking at is sort of revenue concentration, right? I think we've sort of seen...

3:59Nassim Taleb:We're seeing by revenue concentration.

4:00Henrik Grim:So revenue concentration, we'd essentially think about it in terms of how distributed your source of revenue is. If you're a brand that's just coming out, that's selling 95 % of your revenue to one wholesaler, one grocer, that's a lot higher risk for us and for you than if you sit with 10 15 20 relatively easily sort of evenly distributed wholesalers and maybe a little bit of on trade and off trade you distribute a risk and i think we've seen some you know especially recently you know some brands that have sort of gone really deep all in with one particular sort of partner customer and then for different reasons, maybe there's a bit of a black swan, they get pulled out.

4:47Henrik Grim:And then obviously having all your eggs in that basket can put you in a pretty tough spot. So again, that sort of probabilistic thinking of, hey, how do I minimize my risk by making sure that I try to not only go really deep with one, but hopefully spread my risks a little bit, really help me sort of maximize my opportunities, right? Obviously, it's an easy sort of thing to say, but I'd really, it's so clear for some of the ones that we've seen gone through a tough time recently has been that sort of high concentration towards one end of the barbell if you may you essentially have all your eggs on one side of the barbell yeah which can be really high opportunity in terms of growth and size right you're signing this one big grocer and maybe that could be the one that takes you to the stars but if it doesn't happen you're fucked yes yes people we're trying to make hungry into the most

5:39Nassim Taleb:valuable food and drink business podcast on planet earth but i really need your help i want to make this podcast so valuable for you to help you grow your business faster stronger better have way more fun we've got a super short customer feedback uh sorry consumer survey audience survey thing on google forms there's a link at the top of the show notes if you could fill that out it would be so helpful we make this podcast way better for you

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